Tag: M.W=200-300

Related Products of 64115-88-4,Some common heterocyclic compound, 64115-88-4, name is 1-Bromo-2-(trifluoromethoxy)benzene, molecular formula is C7H4BrF3O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

5 rnL microwave vial was charged 4-ethynyl-7H-pyrrolo[2,3-d]pyrimidine (143 mg, 1.0 mmol), l-bromo-2-(trifluoromethoxy)benzene (241 mg, 1.0 mmol), PdCl2(PPhS)2 (35 mg, 0.05 mmol) and CuI (10 mg, 0.05 mmol). 3 mL of anhydrous CH3CN were added, after 10 min of stirring followed by 1.4 mL of Et3N. The reaction mixture was purged with argon for 5 min. Then the vial was capped and placed in a heating block at 60 0C for 18 h. Then it was cooled down to ambient temperature and concentrated in vacuo. The resulting black residue was re-dissolved in 3 mL of DMF and purified by reverse-phase preparative HPLC in CH3CN/H2O system containing 0.1% of TFA. Fractions, containing the product, were combined and partitioned between EtOAc (50 mL) and saturated aqueous NaHCO3 (50 mL). The organic layer was washed with brine (1 x 30 mL), dried over anhydrous Na2SO4 and filtered through a short silica gel plug. The filtrate was concentrated in vacuo to give the title product as a yellow solid (43 mg, 14% yield).[0334] 1H NMR (500 MHz, DMSO-J6): delta 6.63 (d, J = 3.5 Hz, IH), 7.55 (dt, J = 7.5, 1.0 Hz, IH), 7.59 (d, J = 8.4 Hz, IH), 7.67 (dt, J = 8.4, 1.7 Hz, IH), 7.75 (d, J = 3.5 Hz, IH), 7.92 (dd, J = 7.7, 1.6 Hz, IH), 8.79 (s, IH), 12.42 (s, IH)[0335] MS (ES+): m/z 304 (M+H)+

The synthetic route of 64115-88-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TARGEGEN INC.; WO2009/55674; (2009); A1;,
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Electric Literature of 17061-62-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 17061-62-0, name is Bis(4-methoxybenzyl)amine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[09331 N,N-bis(4-methoxybenzyl)ethenesulfonamide, Example 460.1. To1 L round bottomed flask was added bis(4-methoxvbenzvl)amine 12.01 (23.16 g, 90 mmol) and TEA (anhydrous (43.8 mL, 315 mmol)) in DCM (200 mL). At 0 C (ice bath), 2-chloro-1-ethanesulfonyl chloride (10.41 mL, 99 mmol) in DCM (100 mL) was added dropwise with stirring. The reaction mixture was stirred at 0 C for 3 h after completion of the addition. LCMS analysis indicated the reaction was complete. The reaction mixture was diluted with water and extracted with DCM. The organic extract was washed with brine and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the initial material as a light-yellow oil, which was purified by silica gel chromatography (a gradient of 0-60% EtOAc in hexanes), to provide 460.1 (23 g, 66.2 mmol, 74% yield) as a white solid. LCMS-ESI (POS), mlz: 370.1 (M+Na).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Bis(4-methoxybenzyl)amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HEATH, Julie Anne; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KHAKOO, Aarif Yusuf; KOPECKY, David John; LAI, Su-Jen; MA, Zhihua; MCGEE, Lawrence R.; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; YANG, Kevin; YEH, Wen-Chen; DEBENEDETTO, Mikkel V.; FARRELL, Robert P.; HEDLEY, Simon J.; JUDD, Ted C.; KAYSER, Frank; (1266 pag.)WO2016/187308; (2016); A1;,
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Synthetic Route of 701-07-5,Some common heterocyclic compound, 701-07-5, name is 2-(2′-Bromophenoxy)propane, molecular formula is C9H11BrO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

[066] 3-methyl-N-(7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,3,4,S-tetrahydro-1H-benzo[d]- azepin-7- amineprepared in Step 7 was used without further purification.Asolution of 3-methyl-N-(7H- pyrrolo[2,3-d]pyrimidin-2-yl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-amine from Step 7(65 mg, crude, about 0.22 mmol), 1-bromo-2-isopropoxybenzene (57 mg, 0.27 mmol), (trans)cyclohexane-1,2-diamine (7.5 mg, 0.066 mmol), Cul (12 mg, 0.066 mmol), and K3P04 (164 mg, 0.77 mmol) in dioxane (2 mL) was stirred at 120 C under nitrogen overnight. The mixture was diluted with water (5 mL), and extracted with EtOAc (20 mL). The organic layer was washed with brine (10 mL), dried over Na2504, filtered, and concentrated. The residue was purified byprep-TLC to give the title compound N-(7-(2-isopropoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-2- yl)-3-methyl-2,3,4,S-tetrahydro-1H-benzo[d]azepin-7-amine(9 mg, yield: 9%).

The synthetic route of 701-07-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHANGZHOU JIEKAI PHARMATECH CO., LTD.; ZHANG, Jintao; XIANG, Yibin; XU, Wen; JIAN, Shanzhong; (40 pag.)WO2015/143692; (2015); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 59557-91-4, name is 4-Bromo-2-methoxyaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 59557-91-4

General procedure: 4-Bromobenzenamines 1a-c (6.4 mmol) were dissolved in the mixed solvents (2M K2CO3:DMF = 1:1, 24 mL), and then added corresponding 4-substituent phenylboronic acids 2a-h (7.7 mmol) and Pd (PPh3)4 (0.22 mmol) under argon. The reaction mixture was refluxed at 100 for 15 h (TLC monitored the reaction). The reaction was then cooled to room temperature and filtered. The filtrate was added 10 times the amount of water and extracted with ethyl acetate. The organic layer was washed with saturated NaCl solution, concentrated under reduced pressure, and dried to give a crude product. The crude product was purified by flash column chromatography (ethyl acetate/petroleum ether, 1:8-1:5) to afford 1,1′-biphenyl-4-amines 3a-x, yield: 77-95%.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Liu, Jingru; Ma, Ruxin; Bi, Fangchao; Zhang, Fa; Hu, Chaoyu; Venter, Henrietta; Semple, Susan J.; Ma, Shutao; Bioorganic and Medicinal Chemistry Letters; vol. 28; 10; (2018); p. 1825 – 1831;,
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These common heterocyclic compound, 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. SDS of cas: 450-88-4

Intermediate [Example Int15.101 -bromo-2-methoxy-4-(methylsulfanyl)benzeneTo a stirred solution of 1 -bromo-4-fluoro-2-methoxybenzene (4.0 mg) in DMF (40 mL) was added sodium methanethiolate (2.76 g). The mixture was stirred at room temperature for 30 minutes and at 85 C for 2 h. Water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silica gel chromatography gave 280 mg of the title compound.1 H-NMR (400MHz, DMSO-d6): delta [ppm]= 2.46 (s, 3H), 3.82 (s, 3H), 6.74 (dd, 1 H), 6.91 (d, 1 H), 7.44 (d, 1 H).

The synthetic route of 1-Bromo-4-fluoro-2-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; SCHULZE, Volker; KOSEMUND, Dirk; SCHIROK, Hartmut; BADER, Benjamin; LIENAU, Philipp; MARQUARDT, Tobias; WEGSCHEIDT-GERLACH, Christof; SIEMEISTER, Gerhard; PRECHTL, Stefan; WENGNER, Antje; BOeMER, Ulf; WO2011/64328; (2011); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 54314-84-0

To a solution of 3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-4-[2-(4-pivaloyloxyphenyl)ethyl]-1H-pyrazolo[3,4-b]pyridine (1 g) in acetone (10 mL) were added cesium carbonate (0.78g), benzyl 3-bromopropyl ether (0.32 mL) and a catalytic amount of sodium iodide, and the mixture was stirred at room temperature for 2 days. The reaction mixture was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 4/1 – 2/1) to give 1-(3-benzyloxypropyl)-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-4-[2-(4-pivaloyloxyphenyl)ethyl]-1H-pyrazolo[3,4-b]pyridine (0.77g). This material was dissolved in methanol (10 mL). To the solution was added 10percent palladium-carbon powder (0.25 g), and the mixture was stirred at room temperature under a hydrogen atmosphere for 2 hours. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 1/1 – 1/2) to give the title compound (0.54 g). 1H-NMR (CDCl3) delta ppm: 1.03 (9H, s), 1.14 (9H, s), 1.15 (9H, s), 1.17 (9H, s), 1.35 (9H, s), 1.9-2.1 (2H, m), 2.9-3.1 (2H, m), 3.1-3.35 (2H, m), 3.35-3.55 (2H, m), 3.95-4.1 (2H, m), 4.1-4.2 (1H, m) , 4.24 (1H, dd, J=12.4Hz, 1.7Hz), 4.49 (2H, t, J=6.1Hz), 5.2-5.3 (1H, m), 5.35-5.45 (1H, m), 5.45-5.55 (1H, m), 6.03 (1H, d, J=7.9Hz), 6.68 (1H, d, J=4.8Hz), 6.95-7.0 (2H, m), 7.15-7.2 (2H, m), 8.26 (1H, d, J=4.8Hz)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 54314-84-0.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; EP1724278; (2006); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 17715-69-4, name is 1-Bromo-2,4-dimethoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 1-Bromo-2,4-dimethoxybenzene

General procedure: A pyrex test tube containing solid of 1,3,5-trimethoxybenzene (1a, 0.3 mmol), carbon tetrabromide (0.075 mmol), AQN-2-CO2H (0.03 mmol) and dry EtOH (5 mL) was irradiated for 20 h at roomtemperature with stirring by a 21W fluorescent lamp under air. The reactionmixture was concentrated in vacuo, quenched with aq Na2S2O3 and extractedwith EtOAc. The organic layer was dried over MgSO4 and concentrated invacuo. Purification of the residue by flash chromatography on silica gel(hexane/ethyl acetate = 6:1) provided 2-bromo-1,3,5-trimethoxybenzene (2a)(66.8 mg, 90%,) as a white solid.

The synthetic route of 17715-69-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tanaka, Masanori; Kamito, Yuji; Lei, Cui; Tada, Norihiro; Itoh, Akichika; Tetrahedron Letters; vol. 56; 43; (2015); p. 5886 – 5888;,
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Electric Literature of 6358-77-6,Some common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: A mixture of sydnone (1 eq.), aryl halide (1.5 eq.), palladium acetate (5mol %), XPhos (10mol%) and potassium carbonate (2 eq.) in DMF (0.5 M) under an atmosphere of nitrogen was heated at 80 C (for 3-alkylsydnones) or 120 C (for 3-arylsydnones) for 14 h before the reaction was allowed to cool to r.t. and water was added. The resulting mixture was extracted with ethyl acetate:40-60 petroleum ether (9:1) and the combined organic layers dried over MgSO4 and concentrated in vacuo. Flash silica chromatography (eluting solvent 20%-100% ethyl acetate in 40-60 petroleum ether) afforded the target 3,4-diarylsydnones. The compounds could be further purified by recrystallisation from ethanol or dichloromethane/petrol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-2-methoxyaniline, its application will become more common.

Reference:
Article; Brown; Harrity; Tetrahedron; vol. 73; 22; (2017); p. 3160 – 3172;,
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Synthetic Route of 5414-19-7, The chemical industry reduces the impact on the environment during synthesis 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, I believe this compound will play a more active role in future production and life.

Under argon, 100 mg (0.30 mmol) of (4S)-1-(4-aminophenyl)-8-methoxy-N,4-dimethyl-4,5-dihydro-3H-2,3-benzodiazepine-3-carboxamide (Example 53.2A) were dissolved in 4 ml of N,N-dimethylacetamide, and 103 mg (0.44 mmol) of 1-bromo-2-(2-bromoethoxyl)ethane and 0.1 ml (0.59 mmol) of diisopropylethylamine were added. The mixture was stirred at 120 C. for three days. The reaction was added to water and extracted three times with ethyl acetate. The solvent was removed on a rotary evaporator and the residue was purified by flash chromatography. This gave 95 mg (79% of theory) of the desired product.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Bromo-2-(2-bromoethoxy)ethane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SIEGEL, STEPHAN; BAURLE, STEFAN; CLEVE, ARWED; HAENDLER, BERNARD; FERNANDEZ-MONTALVAN, AMAURY ERNESTO; MONNING, URSULA; KRAUSE, SABINE; LEJEUNE, PASCALE; SCHMEES, NORBERT; BUSEMANN, MATTHIAS; HOLTON, SIMON; KUHNKE, JOACHIM; (434 pag.)JP2015/529192; (2015); A;,
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Electric Literature of 53087-13-1,Some common heterocyclic compound, 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, molecular formula is C13H11BrO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: All glassware used in the following procedure was flame dried and then cooled under nitrogen prior to use. A portion (1 mmol) of the required aryl bromide (10.00 mmol) was added to a suspension of magnesium turnings (250 mg, 10.5 mmol) in tetrahydrofuran (12 mL) containing a few iodine crystals and the mixture gently heated whilst stirring vigorously. Once the reaction forming the Grignard reagent had initiated (reflux became self-sustaining) the remaining bromobenzene was added dropwise at such a rate that gentle reflux was maintained. The mixture was then heated at reflux until the magnesium was consumed (usually 30-60 min) and then was cooled for 30 min using an ice bath. A solution of 1-benzyl 4-piperidone (5.00 – 6.25 mmol) in tetrahydrofuran (8 mL) was added dropwise over 1-2 h and the mixture was stirred for 1 h and then the ice bath was removed and the reaction mixture allowed to warm to room temperature whilst stirring for at least a further 2 h. The reaction was quenched by the addition of saturated ammonium chloride solution (60 mL) and extracted into diethyl ether (2 × 30 mL) followed by ethyl acetate (3 × 30 mL). The organic phases were combined and subjected to standard work up conditions to give the required crude product. Purification of the title compound was achieved by flash chromatography on silica or, where indicated, by elution through a short length silica column using the eluant specified. In some cases, the crude piperidinol was dehydrated directly without purification as indicated.

The synthetic route of 53087-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Conway, Richard J.; Valant, Celine; Christopoulos, Arthur; Robertson, Alan D.; Capuano, Ben; Crosby, Ian T.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 7; (2012); p. 2560 – 2564;,
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